CA2101241C - Ciprofloxacine encapsulee dans des liposomes - Google Patents
Ciprofloxacine encapsulee dans des liposomesInfo
- Publication number
- CA2101241C CA2101241C CA 2101241 CA2101241A CA2101241C CA 2101241 C CA2101241 C CA 2101241C CA 2101241 CA2101241 CA 2101241 CA 2101241 A CA2101241 A CA 2101241A CA 2101241 C CA2101241 C CA 2101241C
- Authority
- CA
- Canada
- Prior art keywords
- ciprofloxacin
- mice
- liposomes
- lipids
- antibiotic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 title claims abstract description 97
- 229960003405 ciprofloxacin Drugs 0.000 title claims abstract description 49
- 239000002502 liposome Substances 0.000 claims abstract description 25
- 150000002632 lipids Chemical class 0.000 claims abstract description 16
- 230000003115 biocidal effect Effects 0.000 claims abstract description 12
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims description 5
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 5
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 239000008188 pellet Substances 0.000 claims description 3
- 239000011363 dried mixture Substances 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 abstract description 25
- 241000894006 Bacteria Species 0.000 abstract description 14
- 230000001225 therapeutic effect Effects 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 5
- 230000003834 intracellular effect Effects 0.000 abstract description 5
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 210000004027 cell Anatomy 0.000 abstract description 3
- 230000008030 elimination Effects 0.000 abstract description 3
- 238000003379 elimination reaction Methods 0.000 abstract description 3
- 230000001010 compromised effect Effects 0.000 abstract description 2
- 238000010790 dilution Methods 0.000 abstract description 2
- 239000012895 dilution Substances 0.000 abstract description 2
- 210000001539 phagocyte Anatomy 0.000 abstract description 2
- 241000699670 Mus sp. Species 0.000 description 32
- 238000011282 treatment Methods 0.000 description 10
- 241000589602 Francisella tularensis Species 0.000 description 7
- 229940118764 francisella tularensis Drugs 0.000 description 7
- 238000001990 intravenous administration Methods 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- 150000007660 quinolones Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000011725 BALB/c mouse Methods 0.000 description 2
- 108020000946 Bacterial DNA Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000237537 Ensis Species 0.000 description 2
- 241000589601 Francisella Species 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 208000034784 Tularaemia Diseases 0.000 description 2
- 230000001332 colony forming effect Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 244000000056 intracellular parasite Species 0.000 description 2
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 238000003794 Gram staining Methods 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229940088516 cipro Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 1
- 229960004236 pefloxacin Drugs 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 230000003307 reticuloendothelial effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2101241 CA2101241C (fr) | 1993-07-23 | 1993-07-23 | Ciprofloxacine encapsulee dans des liposomes |
| EP94305331A EP0652008A1 (fr) | 1993-07-23 | 1994-07-20 | Ciprofloxacin encapsulé en liposômes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2101241 CA2101241C (fr) | 1993-07-23 | 1993-07-23 | Ciprofloxacine encapsulee dans des liposomes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2101241A1 CA2101241A1 (fr) | 1995-01-24 |
| CA2101241C true CA2101241C (fr) | 1998-12-22 |
Family
ID=4151982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2101241 Expired - Lifetime CA2101241C (fr) | 1993-07-23 | 1993-07-23 | Ciprofloxacine encapsulee dans des liposomes |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0652008A1 (fr) |
| CA (1) | CA2101241C (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9402845B2 (en) | 2005-12-08 | 2016-08-02 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof |
| US9987227B2 (en) | 2013-10-22 | 2018-06-05 | Aradigm Corporation | Inhaled surfactant-modified liposomal formulations providing both an immediate and sustained release profile |
| US10064882B2 (en) | 2007-05-07 | 2018-09-04 | Insmed Incorporated | Methods of treating pulmonary disorders with liposomal amikacin formulations |
| US10124066B2 (en) | 2012-11-29 | 2018-11-13 | Insmed Incorporated | Stabilized vancomycin formulations |
| US10238675B2 (en) | 2014-05-15 | 2019-03-26 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US11571386B2 (en) | 2018-03-30 | 2023-02-07 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| US12521345B1 (en) | 2018-05-02 | 2026-01-13 | Insmed Incorporated | Large-scale manufacturing methods for aminoglycosides |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972379A (en) * | 1995-02-14 | 1999-10-26 | Sequus Pharmaceuticals, Inc. | Liposome composition and method for administering a quinolone |
| US6221386B1 (en) | 1996-03-08 | 2001-04-24 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence | Use of virulence factors of pathogens to improve liposomal delivery of therapeutic agents |
| ES2130056B1 (es) * | 1997-01-16 | 2000-02-01 | Lipotec Sa | Un nuevo preparado farmaceutico para mejorar la biodisponibilidad oral de drogas de dificil absorcion. |
| US6991807B2 (en) | 2000-02-24 | 2006-01-31 | Advancis Pharmaceutical, Corp. | Antibiotic composition |
| US6565882B2 (en) | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US6667042B2 (en) * | 2000-02-24 | 2003-12-23 | Advancis Pharmaceutical Corp. | Fluroquinilone antibiotic product, use and formulation thereof |
| US6541014B2 (en) | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
| US20020197314A1 (en) | 2001-02-23 | 2002-12-26 | Rudnic Edward M. | Anti-fungal composition |
| AU2004258953B2 (en) | 2003-07-21 | 2011-02-10 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| WO2005009365A2 (fr) | 2003-07-21 | 2005-02-03 | Advancis Pharmaceutical Corporation | Produit antibiotique, son utilisation et sa formulation |
| CA2533358C (fr) | 2003-07-21 | 2014-03-11 | Advancis Pharmaceutical Corporation | Produit antibiotique, utilisation et formulation associees |
| US8758820B2 (en) | 2003-08-11 | 2014-06-24 | Shionogi Inc. | Robust pellet |
| JP2007502294A (ja) | 2003-08-12 | 2007-02-08 | アドバンシス ファーマスーティカル コーポレイション | 抗生物質製剤、その使用法及び作成方法 |
| US8246996B2 (en) | 2003-08-29 | 2012-08-21 | Shionogi Inc. | Antibiotic product, use and formulation thereof |
| JP2007513869A (ja) | 2003-09-15 | 2007-05-31 | アドバンシス ファーマスーティカル コーポレイション | 抗生物質製剤、その使用法及び作成方法 |
| JP2007530639A (ja) * | 2004-04-02 | 2007-11-01 | イタルファルマコ,ソシエダ アノニマ | リポソーム製剤 |
| ES2254027B1 (es) * | 2004-11-26 | 2007-07-01 | Italfarmaco, S.A. | Formulaciones liposomales. |
| US8715727B2 (en) | 2004-07-02 | 2014-05-06 | Shionogi Inc. | Tablet for pulsed delivery |
| US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
| US8778924B2 (en) | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
| US8299052B2 (en) | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
| US8268347B1 (en) * | 2006-10-24 | 2012-09-18 | Aradigm Corporation | Dual action, inhaled formulations providing both an immediate and sustained release profile |
| US8119156B2 (en) | 2006-10-24 | 2012-02-21 | Aradigm Corporation | Dual action, inhaled formulations providing both an immediate and sustained release profile |
| US8071127B2 (en) | 2006-10-24 | 2011-12-06 | Aradigm Corporation | Dual action, inhaled formulations providing both an immediate and sustained release profile |
| US9968555B2 (en) | 2014-04-08 | 2018-05-15 | Aradigm Corporation | Liposomal formulations that form drug nanocrystals after freeze-thaw |
| CN116115576A (zh) * | 2022-12-30 | 2023-05-16 | 成都市妇女儿童中心医院 | 一种功能化的载双药脂质体纳米粒子及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ201010A (en) * | 1981-06-19 | 1986-02-21 | Ciba Geigy Ag | The treatment of inflammation diseases using desferrioxamine |
| WO1991009616A1 (fr) * | 1989-12-22 | 1991-07-11 | Yale University | Antibiotiques a la quinolone encapsules dans des vesicules de lipides |
-
1993
- 1993-07-23 CA CA 2101241 patent/CA2101241C/fr not_active Expired - Lifetime
-
1994
- 1994-07-20 EP EP94305331A patent/EP0652008A1/fr not_active Withdrawn
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10328071B2 (en) | 2005-12-08 | 2019-06-25 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof |
| US9511082B2 (en) | 2005-12-08 | 2016-12-06 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof |
| US9549925B2 (en) | 2005-12-08 | 2017-01-24 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof |
| US9549939B2 (en) | 2005-12-08 | 2017-01-24 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof |
| US9402845B2 (en) | 2005-12-08 | 2016-08-02 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof |
| US10064882B2 (en) | 2007-05-07 | 2018-09-04 | Insmed Incorporated | Methods of treating pulmonary disorders with liposomal amikacin formulations |
| US10124066B2 (en) | 2012-11-29 | 2018-11-13 | Insmed Incorporated | Stabilized vancomycin formulations |
| US10471149B2 (en) | 2012-11-29 | 2019-11-12 | Insmed Incorporated | Stabilized vancomycin formulations |
| US9987227B2 (en) | 2013-10-22 | 2018-06-05 | Aradigm Corporation | Inhaled surfactant-modified liposomal formulations providing both an immediate and sustained release profile |
| US10588918B2 (en) | 2014-05-15 | 2020-03-17 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US11446318B2 (en) | 2014-05-15 | 2022-09-20 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US10251900B2 (en) | 2014-05-15 | 2019-04-09 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US10238675B2 (en) | 2014-05-15 | 2019-03-26 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US10751355B2 (en) | 2014-05-15 | 2020-08-25 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US10828314B2 (en) | 2014-05-15 | 2020-11-10 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US11395830B2 (en) | 2014-05-15 | 2022-07-26 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US10398719B2 (en) | 2014-05-15 | 2019-09-03 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US12377114B2 (en) | 2014-05-15 | 2025-08-05 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US12016873B2 (en) | 2014-05-15 | 2024-06-25 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US12168021B2 (en) | 2014-05-15 | 2024-12-17 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US12168022B2 (en) | 2014-05-15 | 2024-12-17 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| US12290600B2 (en) | 2018-03-30 | 2025-05-06 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| US11571386B2 (en) | 2018-03-30 | 2023-02-07 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| US12521345B1 (en) | 2018-05-02 | 2026-01-13 | Insmed Incorporated | Large-scale manufacturing methods for aminoglycosides |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2101241A1 (fr) | 1995-01-24 |
| EP0652008A1 (fr) | 1995-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |